


Winner Winner

by wildfrancium



Category: Check Please! (Webcomic)
Genre: Aftercare, Anal Sex, Blindfolds, Butt Plugs, Choking, Crying During Sex, Established Relationship, Forced Orgasm, Gags, M/M, Nipple Clamps, Rough Oral Sex, Safe Sane and Consensual, Sybians, Trans Eric "Bitty" Bittle, Trans Kent, Trans Male Character, amab and afab language
Language: English
Status: Completed
Published: 2018-11-30
Updated: 2018-11-30
Packaged: 2019-09-02 15:30:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,626
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16789711
Author URL: https://archiveofourown.org/users/wildfrancium/pseuds/wildfrancium
Summary: Jack and his boyfriends have some fun.





	Winner Winner

**Author's Note:**

> I meant to finish a different thing and wrote this instead. Enjoy~
> 
> Also assume the red, yellow, green system is in place and everything was discussed off camera.

Jack circled his boyfriends. The apartment was loud with the sybians whirring away and the loud moans echoing around the living room. The sybians faced each other, but Eric and Kent were both blindfolded. The way they were positioned, they could both lean forward and please Jack’s cock with their mouths. But at the current moment both of them wore ball gags. 

Spit covered their mouths and dripped down onto their chests making them shiny. Kent’s flat nipples were peaked and flushed and Eric’s perky nipples had been clamped at the beginning. 

Both were completely naked with their legs cuffed to the sides of their sybians and their hands cuffed to the front, each of their left hands were wrapped tight around a small ball with a bell. 

Kent had a fat, little plug stuffed in his ass and Eric had a chain connecting his nipple clamps to the cuffs around his wrists. 

Jack went to Eric first. He knelt and ran hands over Eric’s shaking thighs. Eric moaned as Jack’s hands went up over his back and down his front, yanking at his nipples before sliding over his stomach to where his fat little over sensitive dick sat against the vibrating part of the sybian. Jack rubbed it making Eric squeal and thrash against his cuffs. Eric had been forced through two orgasms and Kent was close to his second. Jack could tell by the way Kent rocked on his sybian.

Jack kept one hand rubbing Eric’s dick in rough circles, while dragging the other lower through his wetness that was leaking all over from being stuffed full on a nice long dildo. It vibrated fast inside his clenching cunt and Jack slid a finger in with it. 

Eric was begging behind his gag, but all Jack did was kiss his cheek and stand up to go to Kent. 

Kent was flushed from head to toe as the fat dildo in his cunt vibrated away. Jack gripped his pecs with sticky hands and groped roughly while Kent moaned louder and louder. 

Jack turned Kent’s sybian up and pinched his fat clit. Kent jerked hard, yelling behind his gag and orgasming for the second time. 

As he panted, Jack ungagged him and shoved two wet fingers into his mouth. Kent licked weakly as he shook and tried to breathe. 

Jack reached over, tugging Eric’s nipple clamps, before undoing his gag. 

“I’m going to move you, Eric,” Jack said before sliding Eric on his sybian across the floor next to Kent. Both of them waited in front of Jack with their mouths open. Jack slid his fingers through their juices and into their cunts and crossed his hands to place wet fingers on each others tongues. 

They sucked each others wetness up eagerly. “Whoever comes a third time first is the winner and I’ll clean them up. The loser cleans the toys and then maybe I’ll clean him up after he shows me he can come a third time,” Jack said pulling his fingers away and standing up. As he undid his belt, both men opened their mouths waiting for his cock.

Jack slapped his hard cock against Kent and Eric’s faces. He slapped his cock on their tongues before roughly shoving into Kent’s mouth. Kent groaned loud, jerking against his cuffs and sucking Jack’s cock eagerly. Jack nudged further in with each thrust, but Kent didn’t like choking. Jack kept his mouth full toeing the line of too much, but knew when to back off. 

When he pulled out and fucked his cock into Eric’s mouth it was different. He pulled Eric’s hair until Eric had taken all of Jack cock and had his nose pressed to Jack’s pubes while he choked, rattling his cuffs hard as his body spasmed and shook.

Jack pulled out and went back to thrusting into Kent’s mouth while Eric coughed and sputtered. When Eric had calmed down, Jack took his hair and fucked back into his messy mouth. Jack held Eric head still as Eric twisted against him. Eric’s spit drooled down Jack’s cock onto his balls and thighs. 

He let Eric go and Kent held his mouth open eagerly. Jack nudged Eric’s sybian to the highest setting knowing how he got when he got a cock all the way down his throat. Eric screamed as Jack went back to fucking Kent’s mouth. Jack and Kent both knew Eric was about to win and it made Kent whine. 

“I know,” Jack said carding his fingers through Kent’s hair. Vibrators could always make Eric come at the drop of a hat. Kent preferred penetration, especially anal, or oral and rimming. 

Jack pulled out of Kent’s mouth and shoved into Eric’s. Eric gagged once and yanked hard against his cuffs as a third orgasm ripped through him. Even Jack could feel it coursing through him as he pulled out. 

Eric was crying hard as Jack turned off his sybian and took off his blindfold. Eric was crying big fat tears, his face was red, and his lips were swollen and slick with spit and precome. Jack smiled at him, kissing his forehead, while he continued to cry. 

Jack took Kent’s blindfold off too and stood back up jerking his cock. Kent looked at him expently while Eric tried to even though he was still crying hard.

Jack came across their faces, trying to get equal amounts on each boyfriend. He groaned at the site of it. “Fuck,” he groaned as he sank to his knees to undo Eric. He turned Kent’s sybian off and undid Kent’s hands. 

Jack lifted Eric up and put him on the floor on his back and turned to Kent glancing to Eric’s dripping sybian. “Clean that up,” he said to Kent up leaned forward to lap up all of Eric’s wetness that had covered the toy.

Jack turned to Eric, he was still sniffling, and spread his thighs. He licked them clean first while Eric dug his hands into Jack’s hair. He spread Eric open wider, pulling swollen lips open to lick away all the extra wetness that had leaked out. 

Eric was moaning when Jack’s tongue licked into his tired cunt, but he howled when Jack closed his lips gently around his swollen dick. Eric pulled Jack’s hair while Jack kept him pinned and sucked his little cock a few times. Eric screamed under Jack until he was out of breath. 

Eric lay panting and Jack crawled up to his face pressing quick kisses to his sore nipples before smiling down at him. Eric looked up at him with bleary, teary eyes, face covered in tears, drool, and come. Jack kissed him hot and hard. Eric groaned weakly, hugging Jack with tired limbs. 

“I love you,” Jack murmured standing and lifting Eric into his arms. 

“I love you,” Eric whispered against Jack’s neck. Jack flicked his eyes to Kent where he had his mouth stretched around he dildo that had been deep inside Eric. 

“I’ll be right back for you,” Jack said cooly making Kent flush. Jack took Eric into the bedroom and did quick clean up before tucking him in.

Jack returned to the living room and moved Eric’s sybian away before freeing Kent. He pulled Kent off and looked at his wet sybian. “Get cleaning,” Jack said sitting behind Kent. Kent started licking and Jack pulled at the plug in Kent’s ass.

Kent gasped as Jack stretched his rim. “Clean,” Jack said with a light slap on his thigh. “And you owe me a third orgasm,” Jack added.

Kent whined, lips around his dildo. Jack pulled at the plug in Kent’s ass again and Kent groaned. He could take way bigger, but Jack didn’t want to overwhelm him.

“Can I sit on your cock and get off?” Kent asked quietly, looking over his shoulder at Jack. Jack looked at his own hard dick and pulled the plug from Kent’s ass. 

Kent scrambled to get lube and slick Jack up just to sink down on his cock with a loud groan and a whimper. He was shaky, face buried in Jack’s neck, while he breathed heavily from being so thoroughly worked over.

“I love your cock in my ass,” Kent whispered. Jack laughed quietly. He wrapped one arm around Kent’s back.

“Anal slut,” Jack said, amused. Kent smiled against Jack’s neck until Jack touched his fat swollen clit. He ass clenched and Jack groaned and groped Kent’s clit more. Kent cried against Jack, shaking and overwhelmed until finally coming again.

“Good boy,” Jack praised releasing into Kent’s ass with a groan. 

“Can...can you plug-plug me back up with your-your come in me?” Kent hiccuped. He leaned back to look at Jack with watery eyes and a come and spit stained face. Jack nodded and kissed Kent’s swollen mouth and stroked his hair. 

“I’m still licking you clean though,” Jack said making Kent whimper. Jack smiled and eased Kent ff his cock. When Kent was plugged back up Jack laid him on his back and spread his thighs. He licked Kent thighs and then deep into his cunt while Kent squirmed and moaned. He sobbed when Jack licked his clit. Jack wiggled the plug in Kent’s ass as he sucked his clit a few times making fat tears roll down Kent’s cheeks. 

Jack licked up his tears with a smug grin while Kent pouted. Jack stroked his hair. “Bath?” he asked and Kent nodded. He lifted Kent into his arms and held him tight. “I’ll get you settled in and then go see if Eric wants to join,” Jack said walking to the bathroom. He pressed a kiss to the top of Kent’s head. “I love you,” he said.

“I love you, too,” Kent replied. 

**Author's Note:**

> I feel like Jack was kinda OOC especially at the end but it's 4:30AM and I don't really care.


End file.
